N-Arachidonoyl-L-Serine-d8

N-Arachidonoyl-L-serine-d₈ (ARA-S-d₈) contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of ARA-S by GC- or LC-mass spectrometry. Arachidonoyl amides of both amino acids and neurotransmitters such as dopamine have been previously reported in the literature.¹ ARA-S is one such recently isolated endocannabinoid with an unusual activity profile. ARA-S does not bind to CB₁ and CB₂ receptors or vanilloid receptor 1. Like cannabidiol , ARA-S (5 mg/kg) antagonizes the hypotensive effects of a 10 mg/kg IV bolus of abnormal cannabidiol in an anesthetized rat blood pressure model.² However, similar to Abn-CBD, ARA-S relaxes isolated rat mesenteric arteries and abdominal aorta, as well as increases phosphorylation of Akt and MAPK in HUVEC.³ The precise mechanisms of action by ARA-S and Abn-DBD in various vascular preparations appears to be different and requires further investigation.

1.Bisogno, T., Melck, D., Bobrov, M.Y., et al.N-acyl-dopamines: Novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivoBiochem. J.351(Pt 3)817-824(2001) 2.Milman, G., Maor, Y., Horowitz, M., et al.Arachidonoyl-serine, an endocannabinoid-like bioactive constituent of rat brain14th Annual Symposium on the Cannabinoids133-133(2004) 3.Milman, G., Maor, Y., Abu-Lafi, S., et al.N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory propertiesProceedings of the National Academy of Sciences of the United States of America103(7)2428-2433(2006)